Depot preparations

Abstract

The invention relates to depot preparations for the targeted release of an aldehyde or ketone together with an alcohol and a carboxylic acid, where the released aldehydes or ketones are organoleptic substances, specifically fragrances or flavorings.

What is claimed is:  
     
         1 . Depot preparations comprising at least one compound of the formula (I)  
       
         
           
           
               
               
           
         
       
       in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
 and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone.  
 
     
     
         2 . Depot preparations according to  claim 1 , wherein, in formula (I) 
 R 1  and R 3 , independently of one another, are a saturated or unsaturated, linear or branched, alicyclic or aromatic radical having 1 to 18 carbon atoms,    R 2  is hydrogen, a saturated or unsaturated, linear or branched, alicyclic or aromatic radical having 1 to 18 carbon atoms,    R 4  is a saturated or unsaturated, linear or branched, alicyclic or aromatic radical having 1 to 22 carbon atoms.    
     
     
         3 . Depot preparations according to  claim 1 , wherein the radicals R 1  and R 2  release an aldehyde R 1 COH or a ketone R 1 R 2 CO which have a molecular weight of from 100 g/mol to 350 g/mol.  
     
     
         4 . Depot preparations according to  claim 3 , wherein the radicals R 1  and R 2  release an aldehyde R 1 COH or a ketone R 1 R 2 CO which have a molecular weight of from 120 g/mol to 270 g/mol.  
     
     
         5 . Fragrances or perfume oils comprising 
 a) depot preparations comprising at least one compound of the formula (I)                           in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
    and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone; and    b) extracts from natural raw materials, hydrocarbons, aliphatic alcohols, aliphatic ketones, aliphatic nitriles, aliphatic carboxylic acids, acyclic terpene alcohols, acyclic terpene aldehydes, cyclic terpene aldehydes, cyclic alcohols, cycloaliphatic alcohols, cyclic or cycloaliphatic ethers, cyclic ketones, cycloaliphatic aldehydes or ketones, esters of cyclic alcohols or carboxylic acids, aromatic hydrocarbons, araliphatic alcohols, esters of araliphatic alcohols with aliphatic carboxylic acids, aromatic or araliphatic aldehydes, ketones or carboxylic acids, nitrogen-containing, aromatic compounds, phenols, phenyl ethers or phenyl esters, heterocyclic compounds or lactones.    
     
     
         6 . Fragrances or perfume oils according to  claim 5 , wherein said fragrances or perfume oils are used undiluted in liquid form or diluted with a solvent.  
     
     
         7 . Fragrances or perfume oils according to  claim 5 , wherein said fragrances or perfume oils are adsorbed to a carrier.  
     
     
         8 . Fragrances or perfume oils according to  claim 5 , wherein said fragrances or perfume oils are microencapsulated or spray-dried or in the form of inclusion complexes or extrusion products.  
     
     
         9 . Cosmetic care products comprising fragrances or perfume oils comprising 
 a) depot preparations comprising at least one compound of the formula (I)                           in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
    and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone; and    b) extracts from natural raw materials, hydrocarbons, aliphatic alcohols, aliphatic ketones, aliphatic nitriles, aliphatic carboxylic acids, acyclic terpene alcohols, acyclic terpene aldehydes, cyclic terpene aldehydes, cyclic alcohols, cycloaliphatic alcohols, cyclic or cycloaliphatic ethers, cyclic ketones, cycloaliphatic aldehydes or ketones, esters of cyclic alcohols or carboxylic acids, aromatic hydrocarbons, araliphatic alcohols, esters of araliphatic alcohols with aliphatic carboxylic acids, aromatic or araliphatic aldehydes, ketones or carboxylic acids, nitrogen-containing, aromatic compounds, phenols, phenyl ethers or phenyl esters, heterocyclic compounds or lactones.    
     
     
         10 . Household products comprising fragrances or perfume oils comprising 
 a) depot preparations comprising at least one compound of the formula (I)                           in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
    and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone; and    b) extracts from natural raw materials, hydrocarbons, aliphatic alcohols, aliphatic ketones, aliphatic nitriles, aliphatic carboxylic acids, acyclic terpene alcohols, acyclic terpene aldehydes, cyclic terpene aldehydes, cyclic alcohols, cycloaliphatic alcohols, cyclic or cycloaliphatic ethers, cyclic ketones, cycloaliphatic aldehydes or ketones, esters of cyclic alcohols or carboxylic acids, aromatic hydrocarbons, araliphatic alcohols, esters of araliphatic alcohols with aliphatic carboxylic acids, aromatic or araliphatic aldehydes, ketones or carboxylic acids, nitrogen-containing, aromatic compounds, phenols, phenyl ethers or phenyl esters, heterocyclic compounds or lactones.    
     
     
         11 . Packaging products comprising fragrances or perfume oils comprising 
 a) depot preparations comprising at least one compound of the formula (I)                           in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
    and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone; and    b) extracts from natural raw materials, hydrocarbons, aliphatic alcohols, aliphatic ketones, aliphatic nitriles, aliphatic carboxylic acids, acyclic terpene alcohols, acyclic terpene aldehydes, cyclic terpene aldehydes, cyclic alcohols, cycloaliphatic alcohols, cyclic or cycloaliphatic ethers, cyclic ketones, cycloaliphatic aldehydes or ketones, esters of cyclic alcohols or carboxylic acids, aromatic hydrocarbons, araliphatic alcohols, esters of araliphatic alcohols with aliphatic carboxylic acids, aromatic or araliphatic aldehydes, ketones or carboxylic acids, nitrogen-containing, aromatic compounds, phenols, phenyl ethers or phenyl esters, heterocyclic compounds or lactones.    
     
     
         12 . Food products comprising fragrances or perfume oils comprising 
 a) depot preparations comprising at least one compound of the formula (I)                           in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
    and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone; and    b) extracts from natural raw materials, hydrocarbons, aliphatic alcohols, aliphatic ketones, aliphatic nitriles, aliphatic carboxylic acids, acyclic terpene alcohols, acyclic terpene aldehydes, cyclic terpene aldehydes, cyclic alcohols, cycloaliphatic alcohols, cyclic or cycloaliphatic ethers, cyclic ketones, cycloaliphatic aldehydes or ketones, esters of cyclic alcohols or carboxylic acids, aromatic hydrocarbons, araliphatic alcohols, esters of araliphatic alcohols with aliphatic carboxylic acids, aromatic or araliphatic aldehydes, ketones or carboxylic acids, nitrogen-containing, aromatic compounds, phenols, phenyl ethers or phenyl esters, heterocyclic compounds or lactones.    
     
     
         13 . Process for the preparation of depot preparations comprising at least one compound of the formula (I)  
       
         
           
           
               
               
           
         
         in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
 and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone;  
 comprising the steps of 
 i) reacting an aldehyde or a ketone with 2 to 4 equivalents of alcohol in the presence of catalytic amounts of acid to give the corresponding acetal or ketal then, under acidic catalysis,  
 ii) cleaving off one equivalent of alcohol from the acetal or ketal, thus giving the corresponding enol ether and subsequent acid-catalysed reaction of the enol ether with a carboxylic acid produces the compounds of formula (I).  
 
 
       
     
     
         14 . Process for the preparation of depot preparations comprising at least one compound of the formula (I)  
       
         
           
           
               
               
           
         
         in which 
 R 1 , R 3  and R 4 , independently of one another, are an organic radical having 1 to 30 carbon atoms,  
 R 2  is hydrogen or an organic radical having 1 to 30 carbon atoms,  
 and the compound of the formula (I), after hydrolysis or enzymatic cleavage, releases an alcohol and a carboxylic acid in addition to the aldehyde or ketone;  
 comprising the steps of 
 producing the compounds of formula (I) by reacting a carboxylic ester or reaction of a carboxylic ester with an organometallic reagent and subsequent scavenging of the hemiacetal which forms with a carboxylic anhydride.